His family—which included his father Zephryn and older brother Gary—moved from Trinidad and Tobago to the city of Burnaby in British Columbia in Canada.

[5] Haywood's ball-handling skills helped him get noticed by former Harlem Globetrotters member Mel Davis, with whom he would begin taking lessons.

[4] In high school, Haywood along with his friends would star in the Notic tapes which were an underground production company based in Vancouver.

Upon joining Langara Falcons basketball team, however, he mainly played as the substitute guard and saw limited minutes on the court.

Haywood has experience playing overseas, primarily in the Basketligaen in Denmark, where he finished the 2014 season as its leading scorer, an All-Star, and a strong candidate for Most Valuable Player.

[12] In April 2020, Haywood signed with the Fraser Valley Bandits of the Canadian Elite Basketball League (CEBL).

[16] Haywood participated in the Kits Youth Basketball League in Kitsilano, Vancouver, British Columbia, Canada in his early teenage years.

With help from former Harlem Globetrotters member Mel Davis, he managed to land a role in the 1997 family comedy film Air Bud, in which he played on main character Josh Framm's team, the Timberwolves.

"[3] Later in the year, he acted as a gang member for an action film directed by Jean-Claude Van Damme, The Hard Corps.

[3] Rainmen owner Andre Levingston commented on Haywood's acting career, "I think it's fantastic that he's had the opportunity to play in a movie.